CD Stacy's First Adventure

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Crossdresser Stacy embraces her sexual awakening.
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CDStacy
CDStacy
32 Followers

I've enjoyed crossdressing for most of my life, but it has been only in the past few years that I have discovered that there is a Stacy inside of me, and have allowed myself the joy of complete transformation: clothes, wig, makeup...the full package. Crossdressing has always been an erotic turn-on for me, and even more so when I am dressed up and completely made up as Stacy.

Even though I am, in general, a hetero-sexual male, attracted to women, I tend to fantasize about men when I am in Stacy mode. The thought of engaging in an act so "womanly", makes me feel electric and alive and sexy and desired. I have never had sexual relations with a man, but Stacy has had very intense fantasies. In fact, in her fantasies, Stacy is a voracious, insatiable vixen, and this is the story of how Stacy made that fantasy come true.

I am mostly in the closet about my crossdressing, and had never gone out in public, until last fall. I decided to treat myself to a transformation makeover photo session. I hired a makeup and photo studio that specializes in transgender services. For my own comfort, I used a service that was out of town, to lower the likelihood of bumping into anyone that I knew.

I planned an entire crossdresser weekend tour: the transformation photo session, as well as a few CD and transgender support groups and social gatherings. Well, the photo session was an absolute dream, and the support groups and social gatherings were really neat. But this story is not about that. This is the story of Stacy's sexual awakening!

I had taken my time earlier that evening, shaving my legs, doing my makeup, and dressing up. I decided to wear something attractive, but not too slutty. After putting on my pantyhose, I wiggled into a tight-fitting, stretchy, black pencil skirt -- something to show off my womanly curves and athletic derriere --flirty, but not too revealing-- and a pair of black patent 5-inch heels. The destination was a gathering of other CD-ers at a local trans-friendly Lesbian bar.

I had a great evening chatting with other girlz. We sang karaoke, and got to know each other a bit. It was fun, but nothing too crazy. I decided not to stay out too late. I had a few drinks, and drove home with a little more of a buzz than I probably should have...especially since I was driving around in a skirt and heels (which was SOO fun, by the way)!

When I got back to my hotel, I had to summon the courage to walk through the lobby. Walking into the bar had been a little easier, as I knew there would be friendly faces on the other side. But who knows who, or what kind of people, I would pass in the hotel lobby! I gathered myself, and made my entrance. Luckily, it was no big deal. I smiled at a few people who passed by, but no one stopped to chat.

Back in my room, I caught a glimpse of a sexy woman looking back at me in the mirror. I looked too good to simply get undressed and go to bed. I decided to fix myself a drink in my room, and show myself a good time. I had a bottle of bourbon, but I had no ice, so I had to go out into the hallway again. I powdered my face, freshened my lipstick, summoned up my courage again, and strutted down the hall to the ice machine.

With my room card in one hand (no pockets in this tight skirt!), and the ice bucket in the other, I sauntered down the entire length of the hallway, in my tight skirt and high heels, to reach the ice machine. I filled my bucket, and as soon as I turned to head back to my room, I noticed a door opening at the other end of the hallway, close to my room. A man stepped out into the hall. When he saw me, he stopped in his tracks.

I decided the only thing to do, was to really go for it. I swung my hips as I glided back down the hall. As I approached the man, I saw that he was a nicely dressed man, in his early 50's or so. As we got a little closer, he smiled at me, and I smiled back. As I passed him, I whispered a quiet, "Hello," and I heard him say the words, "That's wild."

With courage, and perhaps a little alcohol still flowing through my veins, something made me stop in my tracks, swivel around with a little attitude, and ask, "What's wild?"

"From the other end of the hallway, I really thought you were a woman."

"I'm woman enough."

"Woman enough for what?" he asked.

I went for it: "Woman enough to make you feel like a man!"

He didn't have an answer for that, and after a brief silence, I added, "I'm about to make myself a drink, sailor. Care to join me?"

I opened the door to my room, and he followed me inside. I pointed to a chair, and asked him to sit while I poured the drinks.

"Bourbon ok?"

"Perfect."

I knew he was staring at me from behind, checking out my ass while I poured the whiskey. Grateful that I had taken the time earlier that evening to lace up my corset, I worked it. I shifted and swiveled my hips, to rock the skirt and show off my feminine figure, as I worked at the bar. I handed him his drink, and sat across from him on the bed, with my legs delicately crossed, like a lady, while we made small talk.

We finished our first drink, and I asked if he wanted another. Strutting and swiveling and posing, I was becoming a little hot and bothered. I could tell he was really checking me out. "But how shall I make my move?" I asked myself.

When I handed him his drink, he must have been a little nervous, because he spilled a bit on his pants. He stood up to wipe it off, and I seized the opportunity! I quickly grabbed a hand towel, and said, "Don't worry, soldier. I'll get that." I kneeled down on my knees right in front of him, and begun to wipe his trousers with the towel. Luckily, the spill was right in the crotch region, so I made sure to use slow, firm strokes.

"How's that?" I asked.

"Pretty good," he replied.

I could feel his manhood stirring in his slacks, and I decided to push further."I should probably check on the inside, to make sure it doesn't stain," I said nervously.

"Yes, I think you should," he answered, equally unsure.

And with that, I slowly unbuckled his belt, and lowered his fly, enjoying the look of my feminine, manicured nails on his belt and zipper. I was becoming intoxicated by the thought of what was about to occur. I was very nervous, my heart beating out of my chest, as I slipped one hand inside his boxer shorts. I thought to myself, "I hope he has a huge..." but the surprise that I found inside took my breath away. He was not fully erect yet, but I could tell that he was quite endowed, and becoming very aroused.

I looked up at him, with my sexy made up eyes, and smiled, as I slid his underwear down around his waist. He was in good shape, and had a nice body. As I slowly revealed his tool, I literally gasped at the size of it...it must have been about 9 inches...and still not fully hard yet.

I took my time, and enjoyed the anticipation, endorphins buzzing through my brain. I slowly and lightly ran my long fingernails up and down the entire length of his beautiful shaft, and tickled his sizable balls hanging in his undercarriage. I gently cupped his balls, and again looked up and smiled at him, and he smiled back.

"You like that?" he asked.

"Yes. Very much!" I whispered as I finally brought my mouth to his waiting organ. I did not take it all in my mouth at once, but took my time, first kissing the head gently and lovingly with my eyes closed. Then I licked the very tip, and then I licked around the head. I licked my lips moist, then slowly slid my tongue up and down the shaft and felt him twitch with excitement as his cock stiffened further and grew even more. I thought to myself, "His cock is growing, and getting hard because he thinks I am sexy. I am making his cock hard. I am a sexy woman, and I make his cock hard!" The thought made me shiver. It made my heart flutter.

"I'm going to suck your cock now." I said just before engulfing the first few inches into my warm mouth. He moaned as I took him in, and I could feel him growing and getting even harder. "10 inches, maybe..?" I wondered. I couldn't tell exactly, but his cock was big, hard and beautiful. I felt drunk. I almost cried. How long have I dreamt of having a cock in my mouth? At last. At last.

I grasped the lower part of his manly shaft with my left hand, and cupped his balls with my right, and pushed his length further into my mouth. I had not taken even half of his cock, when I promised myself that I was going to take it all. I wasn't quite sure how, but I wanted his cock inside of me, and I was going to find a way to do it.

In the meantime, I slurped and sucked, bobbing my head up and down, while gently squeezing his big balls. I was moaning and so was he. With a long, upward lick of my tongue, I again looked up at my man, and asked, "Do you like that? Am I your cocksucker? Am I your naughty, slutty cocksucker?"

Then I opened my mouth and swallowed a few more inches of his cock. He was quite hard now, and I could not believe how big he was, and how he filled up my mouth. I felt so lucky for him to be giving me his big, beautiful, sexy cock, and yet I felt like I deserved it. It was a gift for me because I was so sexy. Bobbing my head up and down, sliding his cock in and out, I continued to stroke his shaft and caress his balls at the same time, and I could taste his delicious pre-come.

This must have gotten him really excited because it was then that I felt his hand on the back of my head, pressing me down, pushing his cock into my mouth. I loved it. I was going to take his cock and I didn't have a choice.

He slowly slid his piston out of my mouth and back in again. With a gentle but deliberate rhythm, he began fucking my mouth. "He's fucking my mouth," I thought, "He's fucking my mouth with his big manly cock, and I love it!" After a while he slowed and just pushed his cock forward, and pressed my head downward. He kept pressing and pushing until I gagged a little bit. He paused for a few seconds, and then pressed my head down again, and thrust his cock forward, deeper into my open, waiting, hungry mouth.

I was almost all the way down his glorious fuck shaft. I wiggled my head a bit, and relaxed my throat as much as I could, and he thrust his cock forward the final inch. I could now feel my lips against the warm skin of his abdomen, and I could feel his balls against my chin. I had his entire cock inside me, in my mouth, down my throat, and I was in heaven. I looked up again, so he could see my sparkling, sexy, submissive eyes, and that my mouth was absolutely filled with his huge cock.

I enjoyed playing the role of the obedient cock sucker, and I knew that it would turn him on. It felt exquisitely dirty and slutty to me, but it also felt empowering and sexy to have his manhood in my mouth, and his balls in my hands.

When he let go of my head, I rose up quickly, to catch my breath, and saw that his big rock hard cock was sloppy, slippery and glistening. I grabbed it again with my left hand and stroked, slowly at first, then picked up my rhythm. Again, I couldn't believe how big it was --I could barely close my hand around it-- but I loved the vision and the feeling of my sexy, feminine fingers, with manicured fingernails, handling and stroking his huge manly cock.

I felt so excited and girly. I looked up at my lover and asked, "Are you going to come for me? Are you going to give me your big hot sticky load of come? Don't I deserve it?"

"Yes, you do, you sexy, naughty slut. You're a great cocksucker!" he said with a devilish smile on his face, and a twinkle in his eye. He was encouraging me, but I didn't need the push. I was on a mission. I spit on his cock to keep it moist and slippery and I kept stroking wildly, until I could tell that he was getting close. His meat was swelling, and his balls were getting tighter. I ravenously opened my mouth and swallowed his cock again. I didn't want to miss it. I wanted to swallow every last juicy drop of my creamy reward.

I started bobbing my head up and down again, fucking his hot cock with my mouth, when I heard his low, guttural moan starting, and I felt his cock stiffen even more. Caressing his balls more firmly now, to coax them to release their load, I felt his cock swell as he thrust it forward in rhythmic spasms. I felt, and tasted, his hot cream spurting into my grateful mouth, load after load, and I moaned and did my best to swallow every drop.

I couldn't contain his enthusiasm, however, and some come dribbled out the sides of my mouth and ran back down his cock. I licked, gulped and swallowed quickly and hungrily between gasps of breath, licking and cleaning his beautiful cock. He had his release, but I was just getting started.

I couldn't take it anymore, and with the taste of his sticky come still on my tongue, I looked up at him, and I begged him to fuck me. "Please fuck me. I need your cock inside me! I need it. Take me! Fuck me now! Please!"

In a quick, smooth motion, he held out his hands, and helped me to my feet. With his strong hands, he grabbed my hips, swirled me around, and pushed me toward the dresser. He was manhandling me. I was in heaven. He pushed me so I was leaning forward. He forcefully pulled my ass toward him, and even spanked me, playfully, a couple of times. This sent a zing of shivers up my spine.

In the mirror, I could see the intensity in his face as he hiked up my skirt, and pulled aside my pink panties. I handed him the tube of KY Jelly that was sitting on the dresser, and he went to work, lubing up his tool, and my love hole. He poked his thick middle finger into my slippery hole as I moaned to let my lover know he was touching me exactly how I longed to be touched. Then he slipped 2 fingers in and slid them in and out a few times. He was expertly preparing me for his big, sexy penis.

He pulled his fingers out, then suddenly, I felt the plump head of his cock against the opening of my hungry sex hole. He adeptly worked his tool and very gently and slowly slid the very tip of his cock just inside. With a little bit of pressure it popped into my ass, and I gasped. My lover was perfect. He knew that he would have to be gentle at first, and proceed slowly, while my muscles relaxed and became ready to accept his considerable manhood. He held still for a moment, and then slowly and firmly pressed forward. I could barely breathe I was so excited. My heart was fluttering. I couldn't believe that I was taking a cock. I was about to be fucked. Like a woman.

He pressed slowly forward again, and then retreated. It felt so good; I could tell he had done a thorough job with the lube. Gently and slowly he slid a few inches in and out, in and out, as I moaned and shuttered. He held onto my hips, strongly, and I loved being held and being fucked. I was almost powerless now, with his cock inside me and his strong hands holding me tightly.

"Yes. Yes. Like that. Just like that."

He kept pumping, slowly and deliberately, pushing just a little further each time. Oh shit, it felt so good, it took my breath away. Once he knew I was ready, he slid his entire cock fully into my ass, as I took a deep breath. I have fooled around with anal toys before, but nothing had ever felt quite like this. This was heaven. I had never been so entirely filled with cock, and never a living breathing hot, fleshy, rock hard penis, with a living, hot, passionate man on the other end.

"Are you ok, my sexy slut?" He whispered in my ear, groping me up and down my waist and hips and supple breasts.

"Oh yes!" I whispered back. "Fuck me with your big cock. Please, please fuck me. Now." And with that, he proceeded to fuck me...Hard.

He pumped his big, manly fucking cock in and out of my hungry love hole, slowly at first and then picked up his tempo. After a few minutes, he really started fucking hard.

"Oh yes!" I moaned, "Oh yes. Fuck me! Fuck me! Fuck me!" in rhythm with his fucking. He started fucking faster, and harder, and held onto my hips tighter. Oh shit, he was really fucking me now. He was absolutely banging me. I could feel and hear the front of his thighs slapping up against the flesh of my ass. I could feel his big balls slapping against the back of my thighs. Yes! This is what it felt like to be a woman! This is what I have been dreaming about: To be the object of a man's hungry passion and to be fucked wildly like an animal.

He was relentlessly pounding his huge shaft into my ass, and I arched my back and pushed my hips and ass backward to receive him. "Yes! Fuck my ass. Fuck my fucking ass with your big fucking cock! Yes! Like that! Yes! Yes! Yes!"

Since he had already come once, I knew that he would last a while, and I was so happy, because I wanted this to last forever. Suddenly, I felt the familiar, uncontrollable wave start to rise within me. I moaned loudly and rhythmically with his pounding as I reached my big O. I had never before achieved an orgasm strictly from that kind of action, and it felt SOOO intense.

"Oh yes! Make me come! Make me come!" I released. I creamed in my panties. And he just kept right on fucking me, with primal brute force, like a freight train. Oh shit. It felt so good to come and still be getting fucked so hard.

Eventually, his piston slowed, and even though his cock was still so very fucking hard, and even though he was sliding the full length of his big fucking shaft slowly in and out of me, I could tell he was trying to catch his breath. He was still so hot and horny, and needed to release another load. I decided to have mercy and help him out. When he pulled back, I turned around and guided him to sit on the edge of the bed. I grabbed the tube of KY, walked up to him, and I squeezed another blob of lube onto his waiting, hard member, which was standing dutifully at attention for me.

Looking at him face to face, I climbed onto the bed and onto his lap. I straddled him with my smooth, stocking-covered-legs, knees spread on each side of his legs. I pulled his face into my womanly bosom, and I slowly lowered myself, practically impaling myself, onto his massive cock. My sex hole was relaxed and ready from the pounding I had already taken, and I thought that would make it easy to slide his tool back inside of me, but his cock was so fucking big, it took my breath away again.

I wiggled my ass on his lap, and pushed down until I engulfed his full length. It was all I could do to breath, but I loved having him inside me. Wiggling my hips on his shaft, I loved feeling his thick, hot shaft deep inside of me. I lifted his face in my hands, looked him right in the eyes, and kissed him passionately and deeply on the mouth. I lifted myself up slowly, and then dropped down quickly, my tongue in his mouth, still staring in his eyes, again impaling myself on my lover's huge, hard cock.

I whispered in his ear, "I am going to fuck you, until you come again, and spray your man seed deep inside of me." I kept lifting myself, and impaling myself, up and down, on his glorious rock hard cock. His cock was so stiff ---he was still so turned on by me --and that made me feel so sexy and intoxicated.

Up the shaft slowly, then falling down again, with my full weight, his hard cock filling me, again and again. I continued the rhythm, wiggling my hips and my ass to give him extra pleasure. Up the shaft, and downward, up and down. Again and again. I began to moan myself into a trance, exhausted, but on a mission not to stop until I coax the love juice out of my man. After a few minutes, he got so excited again, that he began pushing his shaft up to meet me every time I came impaling myself down.

Soon, he was once again fucking me hard, with deliberate, unrestrained passion. I no longer had to lift myself and lower myself, because he began ramming his cock upward, holding my hips in place, pushing his massive cock up and deep inside of me. He was pumping me hard, getting ready to fill me with hot come. He kept pushing up, ramming his cock into my ass, harder and harder, faster and faster. He moaned and grunted, and his cock swelled once again, and I felt the wet warmth as he pumped his hot, creamy juice deep inside of me.

CDStacy
CDStacy
32 Followers
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